Oliver leads the postal detective team in investigating a letter from ten-year-old boy alerting his grandmother he's running away after they've been mysteriously separated. Meanwhile, the rest of the Dead Letter Office team Shane, Rita and Norman is preparing for the arrival of a new supervisor, the larger-than-life Theresa Capodiamonte, who challenges them to take greater risks to deliver the seemingly undeliverable letters and packages. With Theresa's support, they unravel clues that reveal the boy's life is in danger, and they go the extra mile to find the intended recipient of his letter. Back at the office, Theresa prepares to take a risk of her own, as she realizes she has a lifelong dream she's never pursued and makes her first dance steps in that direction.

The postal detectives are inspired by their supervisor to take a risk to save the life of an Army veteran, as the supervisor gets a turn to sing and dance on stage, realizing it's never too late to pursue life's dreams.

The postal detectives seek out a young rancher who writes a letter to his beloved asking her not to get married on Saturday. What will have transpired when his letter arrives 8 years after he wrote it? Meanwhile, their strict new supervisor is on a journey of her own.

The postables investigate a package from a son to his estranged father. While their tough-as-nails supervisor turns towards a new life chapter. Guest stars Della Reese.

A estranged family feel like they have been given another shot at life when they receive a letter from beyond the grave.

When the postal detectives discover a letter postmarked with a future date, it sets off a chain reaction that leads them down a surprising, emotional journey. As Rita prepares for the Miss Special Delivery pageant-and faces threats from Glynis Rucker (special guest star Marilu Henner), an intimidating supervisor whose daughter is also competing for the crown-Oliver, Shane and Norman find themselves in the middle of a unique couple's struggle for acceptance.

The postal detectives discover a package of music that can launch a career and restore a life. Guest stars Valerie Bertinelli.

Justice comes in the form of a letter as the team at the Dead Letter Office solve clues to deliver not only a letter, but an unspeakable truth that has been buried for years. Guest stars Valerie Bertinelli.

Oliver and Shane have to enter a bank vault full of a life-changing amount of treasure, but it's all part of a case. Rita advances to the next level of the Miss Special Delivery contest.

Norman meets his grandmother for the first time. Meanwhile, the postal detectives try to reunite an estranged family.